


Sugar Me Sweet

by clindzy



Category: Supernatural
Genre: Canon-Typical Violence, Genderbending, Implied Sexual Content, Implied/Referenced Underage Sex, Jealous Sam Winchester, M/M, Mild Gore, Panty Kink, Possessive Dean Winchester, Sam in Makeup, Wincest - Freeform
Language: English
Status: Completed
Published: 2016-03-31
Updated: 2016-03-31
Packaged: 2018-05-30 09:49:17
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 1,794
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6419026
Author URL: https://archiveofourown.org/users/clindzy/pseuds/clindzy
Summary: <blockquote class="userstuff">
              <p>Sam gets insanely jealous of all the girls that take Dean away from him and tries to find a way to capture Dean's attention. In the process, he finds out a secret that Dean has been harboring.</p>
            </blockquote>





	Sugar Me Sweet

**Author's Note:**

> Written for the March Tumblr Writing Challenge, my prompt was genderbending and my partner was plaidandwhiskeydean.

That knot Sam feels when he smells cheap, sweet perfume on Dean isn’t just basic anger; oh, it goes way beyond that. He wants what every push up bra lipgloss wearing, eye lash batting girl in whatever town they’re tearing through that week is getting. From the time he was fifteen, Sam knew he was different, but couldn’t figure out quite how. All he knew he is he loved the remnants of Dean’s long forgotten conquests: fishnets seemingly worn only once, a silk blindfold, a pair of platform black heels, and even a leather miniskirt.

Focused more on hunting and raising Sammy, Dean never noticed those things disappearing. Sam began to wonder if he had ever noticed the blatant calling cards in the first place. So, Sam became more brazen and started buying small feminine items sure to capture Dean’s attention, lip gloss, black eyeliner and tighter t shirts.

Dean finally noticed one late fall afternoon as Sam was hitting the last days of sixteen, kissing seventeen, desperately warring with himself on keeping his own filthy, impure thoughts locked up tight. A broad shouldered senior was strong arming his way through the crowd, obviously dead set on approaching Sam who was exiting his latest unmemorable high school on a tiny dot in the latest stop on the Winchester journey of trying to find the thing that killed their mother.

“Hey, Princess!” The senior football player catcalled, his voice echoed, booming and carrying outside.

Dean immediately lifted his head, his father’s training allowing him to zero in directly on who was harassing his beautiful baby brother.

Sam clutched his backpack tighter, tendrils of anxiety blooming outward from the base of his spine. He knew exactly what Mitchell was looking for; of all days for him to wear his silky boyshorts and black fitted t shirt.

Mitchell lengthened his strides, advancing on him, unaware of Dean’s presence in the parking lot.

“Samantha, let’s see that pretty ass and what’s covering it,” Mitchell cooed, false affection dripping from his voice like daggers.

“Not a chance, Mitchell,” Sam gritted out.

Sam started jogging down the sidewalk, not caring that he looked like the stereotypical weak gay boy or pansy as he’d been called at his last school.  Chancing a look over his shoulder, he saw that Dean had Mitchell flat on the hood of the Impala, arms pinned behind his back, clearly in the midst of a heated physical argument, Dean doing all of the talking, with Mitchell bleeding profusely from his mouth and his right eye.

Sam started sobbing but quieted his cries by shoving his fist in his mouth and ducked behind the dumpster at the far end of the faculty parking lot. He steadied himself by opening his backpack, removing the silk blindfold he always carried with him and smoothed it over his fingers, focusing on the cool texture, the ridges in the strap, and how he wished someday Dean would want to use it on him.

Dean finally released Mitchell from his grip, not with any satisfaction or resolution of his feelings as he realized with a swallow and a knot of something warm and not entirely unpleasant began to bloom in his chest.

Mitchell spat on the ground, blood and spit landing inches from Baby, glaring at Dean. “He was asking for it, you know, dressing like that. Such a tease in those t shirts. What a slut in those fishnets and panties.”

Dean clenched his fists, cracking all of his bloodied knuckles open again, ready to go to blows again with this poor excuse of a human.

Dean opened his mouth and spoke in a low voice, “I suggest if you want to live to see tomorrow, let alone graduate from this podunk high school, you will close that mouth, turn around, go home and not speak to anyone or do anything until I tell you that we’ve left town.”

Mitchell paled, shook his head and backed away slowly to his car. Dean stared the senior down, ice cold lethality projecting full force from his eyes, only turning around to open Baby’s door once he heard the weak exhaust of the Mitsubishi Eclipse sputter out of the main parking lot, and finally turning into traffic.

Dean slammed his door shut behind him, banging his abused fists against the steering wheel, cursing his failed efforts at sparing Sam the pain and experiences he’d faced just a few short years ago but had been far too embarrassed to talk about. Par for the Winchester course – why talk about it when you can bury it with alcohol, women and killing anything evil that moves?

Cheeks dry and mouth steady, Sam fumbled in his backpack with his numb fingers, searching, seeking, breathing out a sigh of relief when he found the black nondescript nylon pouch holding his most personal, private items. Gripping his treasured juicy pink lipgloss in his right hand, Sam feels the frisson of anxiety of lessen as he unscrews the top, swiping the tip across his lips, coating his lips in the familiar sticky substance. It’s bittersweet as he touches his cheek, thinking of the countless times before he’s envisioned a different material touching his lips; Sam swallows hard against the tears that threaten to fall. He reaches inside the pouch again, this time holding his prized kohl black eyeliner. By feel alone he lines his eyes knowing instinctively how to make them appear even bigger than normal. Sam sees the way Dean gravitates towards all those doe eyed girls. He knows that he has what Dean wants; he just has to get him to see it. Feeling like he can breathe somewhat normally, Sam puts his makeup away and stands up, smoothing his shirt out, ready to face what awaits him.

Dean tore out of the parking lot, tires squealing in protest, hellbent on finding Sam. Why had he kept all of this from his perfect, intelligent, gorgeous baby brother for so long? He was stupid, foolish and so very selfish. Just as he got to the edge of the school’s athletic complex he saw Sam’s determined stride, headed towards their motel. Dean steeled himself for any number of possibilities that lay in front of him: losing Sammy forever, being seen as a monster by his own flesh and blood, or possibly, the scariest of all, that Sam wanted him that way, too, and he wasn’t a sick, demented soul bound for hell.

Sam heard the familiar growl of the Impala long before Dean caught up to him. He chewed his bottom lip nervously, the artificial cotton candy taste hitting his tongue like a shock. He was scared now that he had seen Dean defend him for his less than conventional interests. Dean had always come across like a typical testosterone charged alpha male – sex was meant as a pursuit between a guy and girl and he was always apparently down to try anything new. Sam itched to pull out his lipgloss again or stroke the blindfold in a quiet spot. Before he had time to get lost in his fears or his thoughts, Dean was swinging Baby’s door open.

“Sammy, get in,” Dean ordered.

Sam gulped and tossed his backpack into the backseat. He knew that tone of voice all too well. He was simultaneously turned on and terrified.

“Obviously, there are some things that we need to clear up.” Dean looked over at Sam, letting his gaze linger over his brother, barely holding back a moan at how gorgeous he looked at that moment.

Sam blushed under the intense scrutiny, fidgeting and squirming as if he was in elementary school all over again, Dean reminding him of Winchester standard operating procedure in that steel laced voice.

“I’m guessing it has something to do with Mitchell,” Sam said quietly, still not meeting Dean’s eyes.

Dean let his right hand drift closer to Sam’s thigh, hoping to imply his meaning without words.

Instead, Sam started shaking, gulping in shallow breaths, fingers opening and closing involuntarily in a clutching motion.

Without a care to the Impala’s paint job or suspension, Dean jerked her off the road and slammed the car into park, unable to take his brother in this soul wrenching pain.

“Sammy, talk to me,” Dean pleaded, thumb stroking his cheek, his cracked knuckles finding sweet relief in the silk of Sam’s chestnut and cinnamon highlighted locks.

“Need my b-b-bag,” Sam stammered past the panic and tears lodged deep in his chest.

Dean turned around, finding Sam’s backpack on the floor, handing it to him, not really sure what it contained that would help to bring Sammy back to him but he would do anything to ease this dam of invisible blood that was oozing out in front of him, leaving his Sammy unrecognizable to him.

Sam’s fingers faltered twice on the zipper before he was able to get it open, delving to the bottom, teeth digging sharply into his lip until he felt the slick pouch in his hands. He simply sat there holding it, waiting for Dean’s reaction.

“What is that, Sam?” Dean asked cautiously.

“This is what I use to make myself feel pretty, D. I’d hoped by now that you would have noticed; the fishnets, the silk blindfold, the heels and that leather miniskirt those _girls_ left behind,” Sam said bitterly, disdain obvious in his tone.

He continued, “When those going missing from your bag didn’t get your attention, I started exploring. It was small at first, the tighter t shirts, then the lip gloss and eyeliner until I moved to outright buying girl’s underwear. My favorite to wear is boyshorts, by the way.”

Sam raised his eyes, tears brimming from his blue green kaleidoscope eyes, meeting Dean’s verdant eyes head on.

“Fuck, Sam.”

Dean hung his head in shame. No one else on the face of the planet could affect him the way Sam could. He owed him an explanation that words would never do justice but he wasn’t sure that his baby brother would allow him such intimate contact at this moment.

“Do you trust me, baby boy?”

Sam colored at his childhood nickname, taken aback at the new sensation it brought: shivers and his balls drawing up against him, cock pressing against his favorite panties, straining to find their way out of his hand me down jeans.

“I always trust you, Dean.”

“You’re not the only one who enjoys these things, Sammy,” Dean whispered, scooting across the bench seat, heady from the rush of knowing Sam felt the same way.

Sticky with gloss and spit, Sam leaned in for a kiss, sighing into Dean, shuddering as he felt pressure at the nape of his neck.

Maybe one of his dreams would come true after all. 


End file.
